Alcatraz, surrounded by treacherous waters, outfitted with the latest security technology, and strictly managed, was reputed to be “escape-proof.” A successful escape has never been confirmed. There were 14 separate escape attempts involving 36 inmates. Of those, 23 were recaptured, 7 shot and killed as they fled, and at least 3 drowned. Five inmates involved two separate escape attempts, two in 1937, and three in 1962, remain unaccounted-for.

Some escape attempts were violent. In 1938, three inmates working in the prison factory killed Officer Royal C. Cline with a hammer, broke through a window, and climbed to the roof. Before they could escape, an officer in a guard tower opened fire on them, killing one and subduing the others.

In 1945, an inmate took advantage of the fact that Alcatraz did the laundry for West Coast military bases. Considered a minimal escape risk, he was assigned to dock duty unloading vessels transporting military laundry to the prison. Over time, he stole one article of clothing at a time from the shipments, until he had assembled a full military uniform. Then he hid under the dock, put on the uniform, and jumped on a boat that was casting off. Officers noted the inmate’s absence immediately. They radioed the ship to return to Alcatraz, and the escape attempt was foiled. Another inmate worked for most of 1962 to loosen a bar in a storage room window. He greased himself with lard so that he could squeeze through the opening. He swam from Alcatraz to the mainland. He was so exhausted that he collapsed on rocks near Golden Gate Bridge and slept soundly until he was discovered an hour later and recaptured.

In 1946, the Alcatraz “Blastout” occurred when six inmates overpowered an officer and stole his keys. They broke into a barred “gun gallery” and captured weapons. Once they realized that the keys didn’t work on any doors leading out of the prison, and that other inmates wouldn’t help them, they took several officers hostage. This set off a gun battle that lasted nearly 2 days before prison officers, aided by U.S. Marines, retook the cell house. Officers Harold Stites and William Miller, and three inmates were killed during the siege. The three recaptured inmates were tried for murder. After their convictions, they attempted escape. Two were executed and one sentenced to 99 years in prison.

The only three inmates not accounted for after trying to escape were John Anglin, Clarence Anglin, and Frank Morris, who broke out together in June 1962. They, with Allen Clayton West, spent several months fashioning crude electric drills and other tools from objects stolen from the kitchen, workshops, and other parts of the prison. They bored holes into the utility corridors behind their cell walls. They built rubber rafts out of raincoats, and used toilet paper, cardboard, cement chips, and human hair from the floor of the barbershop to create fake human heads. On the night of June 11, they placed the dummy heads in their cots to make it appear as if they were present and sleeping. West never made it out of his cell in time. The Angwins and Morris crawled through the holes in their cell walls, climbed up the pipes of the utility corridor to the ceiling, and, carrying their rafts and homemade paddles with them, escaped through a ventilator shaft to the roof. Then they made their way down the wall of the cell house to the beach, and plunged into the water.